A substantial body of research suggests that the decision to drop out of school is not made suddenly nor stems from recent and potentially temporary factors (Bridgeland, DiIlulio, & Morison, 2007). Rather, the decision to drop out is part of a long process of disengagement from school with initial risk indicators evident in elementary school (Barrington & Hendricks, 1989; Christenson, Sinclaire, Lehr, & Godber, 2001) and even prior to school entry (Jimerson et al., 2000). Few studies, however, have examined risk indicators that occur prior to school entry and during early schooling that may predict disengagement in the elementary school years. This early disengagement may represent the genesis of the process of disengagement from school and ultimately school dropout. At present, there is little empirical research on its nature and course, even though disengagement from elementary school is highly correlated with disengagement in middle school (e.g., Gottfried et al., 2007; Skinner et al., 1998) and high school (Gottfried et al., 2001; Marks, 2000; Otis et al., 2005), which is predictive of school dropout (Archambault, Janosz, Fallu, & Pagini, 2009). In the proposed study, we focus on early childhood malleable factors in the home, within the child, and within the school setting that can set children on an early trajectory of school disengagement. We adopt a multi-level perspective by examining the roles of children's early home environments and early self-regulation behavior in predicting student engagement in 3rd grade. Specifically, we examine the role of household chaos experienced from birth to age 5 and child self-regulation ability at Kindergarten (K). We also propose to examine whether high classroom quality across the early elementary school years (K through 3rd grade) can help to mitigate the detrimental effects of early chaotic home environments and self-regulation difficulties on later student engagement. We will use a structural equation modeling framework and multi-method multi-informant data (observational, teacher-report, and/or child-report) to derive latent variables of our major constructs of interest, including child self-regulation, studet engagement, and classroom quality. A major strength of this study will be the inclusion of a wealth of covariates to help strengthen inferences, including income, race, gender, age, parenting, parent education, and child early reading achievement. These data will be drawn from an epidemiologically-derived sample (N=1,292), with oversampling of poor and African American families, which presents an unprecedented opportunity to examine these associations in a large, diverse, and at-risk population.